Peter Aprile

Founder, Counter Tax Lawyers
Called to the bar in 2006

Peter Aprile has always found the legal profession to be behind the curve — even as a law student, more than a decade ago, at Queen’s University. “We didn’t have a place for students to access the entire Income Tax Act electronically,” recalls his former tax professor Kim Brooks. “Out of love for the subject, Peter loaded an electronic version onto a CD-ROM.” Aprile’s urge to merge law with technology never faded.

After graduating in 2005, he articled at Fitzsimmons & Company, a four-lawyer tax firm in Toronto. He got hired back as an associate, but, three years later, the firm’s founder, Richard Fitzsimmons, had a heart attack. He died soon after. Losing his mentor left Aprile heartbroken. “I will always owe Richard a debt.”

With Fitzsimmons & Company gone, Aprile decided to launch his own firm. Now called Counter Tax Lawyers, its office is in Toronto’s Summerhill neighbourhood, “right around the corner” from the 40-year-old’s home, where he lives with his interior-designer wife and their two young children. It now stands as a leader in tax-dispute litigation — largely because of how heavily Aprile invests in cutting-edge technology.

“If you want to survive in any industry, you better be doing something different and you’d better be doing it better than everyone else,” says Aprile. His claim to fame is building proprietary software that simplifies and streamlines complicated tax files — an industry first.

“I think that Richard always knew that I was going to create something new,” he adds. And he has proof: after Fitzsimmons hired Aprile, he gave him a copy of his book on tax law, adding an inscription that reads, Commit the entirety hereof to memory, and then forget it all and write your own story. “I read that inscription a few times a year and smile.”

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Photography by Ian Patterson, hair and makeup by Jessica Haisinger, shot on location at Cluny Bistro & Boulangerie.